If the websites are developed using ASP, FrontPage, ASP.NET environment, Windows Streaming Media, Access, MS SQL Server or any of the other Microsoft’s owned technologies then you should consider Windows hosting for yourself. As the websites of your friend are developed using ASP then your friend should opt for Windows hosting only. ASP is not supported with Linux hosting.
It is not necessary to have a Dedicated server if you have multiple domains. Infact, according to your description about the traffic of the websites of your friend, I would recommend your friend to choose a Windows VPS package for himself. Windows VPS will offer you almost the same features as Windows Dedicated server and costs much less than a Windows Dedicated server.
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